coworkers want shirts with our boss’s face on them, disastrous ex-business partner and I were just hired at the same company, and more

It’s five answers to five questions. Here we go…

1. My coworkers want to wear shirts with our boss’s face on them for Boss’s Day

A person at my work (an elementary school, to give you an idea of the culture) has suggested that, for Boss’s Day, everyone buy a $10 Hawaiian shirt printed with my boss’s face, and that we all wear them on Boss’s Day. She’s said if money is a problem, a parents club can cover our costs.

Here are my issues: (1) I find it deeply creepy to own clothing with my boss’s face on it, (2) I hate the idea of buying a fast fashion shirt that I will certainly wear once and then throw away, because, again, creepy, and (3) I can absolutely afford $10, and they’d cover it anyway, so that takes away the socially graceful excuse.

People are already reply-all’ing: “I’m in!” “How fun!” Is there any way I can get out of this without being a complete killjoy?

I’d think the fast fashion argument might hold the most sway, so you could try replying-all with, “I’m probably not the only one trying to avoid fast fashion clothing that I’ll only wear once, so I wonder if there are other things we could do instead.” (Extra points if you also add, “And Boss’s Day is kind of weird to begin with — I’d think we could just skip it without Jane caring.”)

2. My disastrous ex-business partner and I were just hired at the same company

Six months ago, I was contacted by a senior employee at a company, asking if I would be interested in a position in a speciality field I studied in grad school. I accepted and am thrilled with the opportunity. It begins in a few weeks.

My skip level boss has set up a meeting with the director of the department and the two new hires for our first day. In that meeting email, I discovered that the other new hire is my former business partner, Jane. We did not part on good terms. Here are some of the highlights:
* Jane set up a duplicate business account at a bank and we got flagged for possible terrorism and money laundering under the Patriot Act. I was not aware she opened a duplicate account under our business name until the bank alerted me. We had to close both accounts and use a different name for the business in financial records.
* She was in charge of the business phone and returning calls, I was in charge of email. Once, she stopped checking voicemail and answering calls for three months. When I asked her if we had any new referrals via phone, she would say, “Nope, nothing.”
* She tried to persuade me to sign up for a joint banking account and combine our finances despite a contract to keep finances separate for two years. She wanted me to help subsidize the cost of a large piece of equipment and because my work incurred more expenses than hers did she wanted to be able deduct my expenses on her taxes. I tried to explain that’s not how all of this would work and she ended up saying, “What is the point of being in business with you if it doesn’t save me money?”
* A month later, Covid hit. When the PPP program came out, I applied and discovered Jane had included me in her application for the PPP, and I was denied for duplicate request. Jane never returned to our office again. Our joint business lasted just shy of two years.
* After parting ways, we ended up being scheduled on a joint presentation for a client we shared. A week before, Jane let me know she was not going to be at the presentation, hadn’t told the client, as she knew I could handle the responsibility and take it over solo.

Since then, I have avoided Jane. We have managed to be publicly amicable. The bottom line is, she is great with clients, just horrible with all other aspects of a business. Years on, she recommends clients to me that fit my specialty and I have begun again recommending clients to her. It’s been almost seven years since we stopped being partners.

For this new position, in theory, we will not work together and possibly not even see each other. Neither of us will be managing each other. For both of us, there is the possibility of moving up to managing more projects with clients in the same department, but slightly different content areas.

No one except my spouse knows the whole backstory of our failed partnership. I’ll be talking to my therapist about managing the butterflies I feel about working with her. But professionally speaking, what is the protocol here? Is it okay to just say we’ve worked together in the past and not go into any details? Is that even something I need to mention? What is my responsibility to HR and my director?

Yes, you can just say you’ve worked together in the past so know each other professionally and leave it at that. You’re not obligated to get into the details of your experience with her or your assessment of her weaknesses.

It would be different if you were a longer-term, existing employee at this company and they were thinking of bringing on Jane. In that case, you’d have the standing (and in many positions, the obligation) to share your assessment from your first-hand experience working with her. But you’re brand new so you don’t have that obligation. You can just leave it at “worked together in the past.”

3. I work in person as a consultant and am frequently left out of things

I have a long-term contract with a team of about 12 people who are all full-time staff. For the most part, I enjoy this role, and the team provided me with my own office on site so that I can better collaborate with them on the project I was hired for.

However, the organization has some pretty strict policies about delineating between staff and contractors, and occasionally this bleeds into the way I’m treated. I am often the last to know about changes or updates to the program because I am not included in the weekly team meetings or all-team emails. The team goes to lunch together or on occasional outings together, and I am not invited. The thing I can’t seem to let go of is a small party they held to celebrate a major milestone on a project that I was specifically hired to manage. I was right down the hall and had no idea.

None of this would matter so much if I didn’t work in person with these folks, and generally, they are warm and friendly people who are happy with my work. Based on how our interactions are otherwise, I don’t think they are being malicious in excluding me from these things, but exiting my office to a completely empty building and realizing that everyone went to lunch together without me does leave me feeling pretty bad.

There’s talk about extending my contract, and I’m tempted to bring this up. Should I say something, or let it go? And how do I approach this without making it sound like I just want a free lunch?

It’s a legal thing, not them being jerks.

Legally, they’re required to treat contractors differently than employees in a bunch of ways. There’s not a clear law saying “don’t invite contractors to office parties” but the government looks broadly at whether there’s any significant distinction in how the company treats employees versus contractors — and if there’s not, there’s a risk the government will decide the contractors should have been employees the whole time, and then the company will owe penalties and back taxes. (In fact, there was a huge thing a while back when the IRS reclassified a slew of contractors at Microsoft as employees because they’d worked there so long and were essentially being treated as employees, and Microsoft had to pay millions of dollars to those contract workers and give them the same stock options as employees.)

So a lot of companies play it safe and delineate between contractors and employees in the ways you described. You’ve got to just accept it as part of working as a contractor.

4. When you need to work for the person who you lost an election to

I live in a rural, very red small town where most county seats are decided during the primaries. This year we had two people running for county clerk, “Roy,” who previously worked in the county clerk’s office , and “Ted,” who currently works there.

This being a small town and Facebook being what it is, the campaigning got a little ugly. As far as I can tell, it wasn’t from the candidates themselves but their supporters. There were posts directly attacking one of the candidate’s (adult) children, posts filled with rumors about impropriety within the current office, etc.

Ted lost by a slim margin. Roy won’t take office until January 1 but I wonder what you would advise Ted to do. Stay in the job he currently has, knowing his new boss just beat them in an election? Start looking for a different job now? The stakes seem a little higher (and much more personal) since it was an election versus two coworkers vying for senior job and one getting it.

I know this answer depends a lot of Ted’s state of mind and how they feel, but if you were Ted what would you do?

It doesn’t just depend a lot on Ted’s state on mind; it depends entirely on Ted’s state of mind. If he doesn’t want to work for Roy after such an ugly campaign, he should start job searching now. If he can attribute the ugliness to Roy’s supporters and not Roy personally (or to the heatedness  of the campaign in general) and thinks he’ll be fine working for Roy — or isn’t sure but is willing to wait and see how it goes — then he doesn’t need to do anything now. There’s no general answer because it’s entirely up to Ted and how he feels about things.

There is an answer for Ted’s coworkers though, which is to not make things weird for either of them and to act as if of course it’s fine for Ted to stay if he wants to, so that he doesn’t have to include “dealing with other people’s weirdness” in the factors he’s considering.

5. Leaving with customer information on your own devices

I’m a mobile caregiver and, for the first time, working for a company that makes me use my own personal phone and devices. As a result, I am accumulating a large and valuable pile of detailed customer information. I am also at the point in my career that I’m working on starting up my own company, which will likely be direct competition.

Normally, I always gladly turn over any devices and all their data without deleting or poaching when I leave a job, but what are the (U.S.) legal rules and norms for when it’s on my own personal devices because that’s all there is? Even if I wanted to, I don’t know if I could delete every one of the many, many customer contacts buried between friends, family, and takeout. I do not know if there exists an official policy as I was never given an employee handbook, and it’s far too awkward to ask.

The rules aren’t any different when business info is on your personal devices: it’s still owned by the employer, and they can still require you to turn it over and remove it from your devices when you leave (even if you were using personal devices because they didn’t supply work ones). If you used their customer contact info at a new job or to start your own business, they could take legal action against you to force you to desist and could sue you for punitive damages as well. It’s not worth trying it.